I Dare You
by JM.Fanatic
Summary: Series of dares performed by the chipmunks and chipettes
1. Chapter 1

So, here I am again with another story and I haven't even updated the two I'm already working on. Am I a procrastinator or what? Well anyway, I'm going to make short drabbles of the chipmunks and chipettes doing dares. We're going to see how well this works out…

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**Dare #1-Kiss Him**

"I dare you to do it," Alvin whispered to Brittany.

Brittany shook her head. "I refuse."

"Come on, Brittany, since when do you turn down a dare?" Eleanor asked.

"Since you two want me to do something like this," she said.

Alvin rolled his eyes. "You act like you've never done something like this before," he said.

"Ssh," someone said from the table across from them and Alvin huffed and rolled his eyes.

"Yes, but I've never done it with someone like him," Brittany argued.

Alvin arched an eye brow. "What's wrong with him?" he asked.

"Ssh," came that person again and Alvin glared at them.

"Really, Brittany, what is wrong with him?" Eleanor asked. "He's really sweet, and caring, and cute, and-"

"Ok, I think she gets it," Alvin interrupted and Eleanor smiled sheepishly. Alvin shook his head and looked at Brittany. "What she's trying to say is that you could do a lot worse," he finished.

Brittany rolled her eyes and looked over at the table where he was sitting. She had to agree with Eleanor with what she said, but come on, it's Theodore. She then realized that Alvin was right; she could do a lot worse. She huffed and looked back over at Alvin and Eleanor. "Alright, fine, but neither of you better say a word about this. I mean it," she warned.

Alvin raised his right hand. "Scout's honor," he said with a smile. Brittany eyed him for a moment before rolling her eyes and getting up and making her way over to Theodore's table. Alvin stood as well. "Come on," he said to Eleanor. "I want a better look." He and Eleanor went and sat at the table behind the table Theodore was sitting at.

Before Brittany get to the table, she looked over the other two. They motioned for her to sit and get moving. She blew out a breath before flipping her hair over her shoulder and continuing to the table. She turned a chair that was beside him to face and took a seat. "Hi, Theodore," she said sweetly.

Theodore slowly looked up and blinked a few times when he saw that it was Brittany. "Uh…hi," he said in an unsure voice.

Brittany really didn't know what to do after this point since she didn't plan on doing it in the first place. She shifted her eyes and then looked around for something to talk about. Her eyes fell on his books and she smiled. "What are you working on?" she asked, succeeding in sounding like she was interested.

Theodore eyed her. "Research for a history paper," he said slowly.

Brittany nodded. "That's nice." She shifted her eyes again. "So…"

"So…" Theodore repeated as he continued to eye her. He had no idea why she was sitting there or what she was up to. She usually wouldn't just come up to him and start making conversation, so he was a bit skeptical.

Brittany was at a loss. She knew she should've planned ahead. She looked over at Alvin and Eleanor, who were telling her to keep going. She rolled her eyes and looked back at Theodore, who was now looking at her with a confused expression. He noticed that she was looking behind him, so he started to turn around to see exactly what she was looking at but she quickly leaned forward and grabbed his shoulders, stopping him. "Wait!" she exclaimed, just to get shushed by people from nearby tables. She rolled her eyes.

Theodore looked a bit shocked. "What?" Brittany smiled, thinking that this was the perfect time to do what she actually came over there to do. She lifted a hand of shoulder and placed it on his cheek, earning look of surprise and worry from him. "What are you doing?" he asked.

Brittany found the way he was looking at her pretty cute as she continued to smile at him. She then gently stroked his cheek. "I actually just realized something," she said.

"And what's that?"

"I think you're actually pretty cute."

Theodore's eyes widened after hearing that. "Ok, who put you up to this, because this isn't funny," he said.

Brittany shook her head. "I'm not trying to be funny. I'm telling the truth. I think you're cute. Is something wrong with that?"

Theodore pulled her hand off his face. "Well, no I guess not, but it's just not like you at all. I don't know if I believe it."

Brittany smirked as she stood. Theodore looked at her, confused. "Well, maybe what I'm about to do will help you out a bit," she said. And then, much to Theodore's surprise, she sat on his lap, put her hand back on his cheek, and then she pressed her lips against his. His eyes widened, as well as the two watching them

Eleanor gasped happily while Alvin smirked. He pulled out his cell phone and snapped a picture. Eleanor looked at him and he smiled. "For evidence," was all he said and she simply rolled her eyes.

Brittany pulled away and laughed when she saw Theodore's face. "Do you believe me now?" she asked.

He opened and closed his mouth, but he was at a loss for words. "Uh…um…I, uh…wha..?" was all he could get out.

Brittany laughed again. "It's a yes or no question, Theodore. It requires a nod or shake of your head."

Theodore just stared at her, trying to process everything. The fact that Brittany said he was cute, that she's sitting on his lap, that she just kissed him. His mind was swirling with confusion of why she did all this to begin with, but since he couldn't exactly talk at the moment, he would have to ask her later. As of now, he answered her question with a nod.

She smiled, and then playfully glared at him. "Then why didn't you kiss me back?" she demanded

He blinked, and then shifted his eyes. "Um…I'm sorry?" he asked, finally getting his words back.

She nodded. "That you are. Now, let's try again." And with that, she kissed him again. It still took a second, but Theodore finally kissed her back.

Alvin's eyes widened slightly. "Whoa, she really gets into her dares, doesn't she?"

Eleanor smiled. "I don't think she's even doing the dare anymore," she said softly.

Alvin looked at her, and then back at the two. He then smiled. "I think you're right."

"Ssh," someone said.

Alvin growled angrily and huffed. "I hate libraries," he mumbled.

--

Well, there you go. How was that? A little rough, I know, but I'm sure I'll get better as I go. Well, now you're in control. Tell me what dares you want me to create with (dare I say it) any couple and let's see how this goes…

Jade


	2. Chapter 2

Here we go. More dares. Let's see how this goes…

--

**Dare # 2- Chili Peppers**

**&**

**Dare # 3- Crush**

Eleanor was sitting at the kitchen table with Alvin in the Seville home. They didn't have much to do as they sat there talking about whatever came to their minds.

"So…" Alvin started and Eleanor just looked at him. "…nice weather we're having," he finished. Eleanor arched an eye brow as she continued to stare at him. "We could use some rain," he added.

Eleanor looked out the window, and then back at him. "Alvin, it is raining," she pointed out.

He looked out the window, and then shifted his eyes. "Oh, well look at that, it sure is…"

Eleanor laughed and shook her head. "God, Alvin, can't you think of anything to do?" she asked. "This is really boring."

He began to think hard, determined to find something to do. Suddenly, he gasped and smiled at Eleanor. "I got it!"

"Well, what is it?"

"Let's play truth or dare…without the truths." He smiled.

Eleanor eyed him. "I don't know…" she said cautiously.

Alvin smirked. "You don't trust me?"

She shook her head. "No."

He laughed and gave her a peck on the lips. "Oh, don't worry. I won't make you do anything too bad," he assured her.

"And yet I'm still worried," she said and he laughed.

"So, let's get started. You go first," he said.

Eleanor thought about it. She stood and went to the cabinets. She looked through a few before gasping in delight and pulling a jar down. She sat down again and placed the jar in front of Alvin. "I dare you to eat at least three of these," she said with a smirk.

Alvin looked down at the jar and his eyes widened when he saw that they were red hot chili peppers. "Ellie, I'm not eating those," he said.

She nodded. "Yes you are."

He looked up at her. "Do you want me to die?"

She laughed. "You're not going to die. It's just three…or more if you choose." She smiled.

Alvin looked down at the peppers again with a nervous expression. Then he slowly reached up and took off the lid. Eleanor smiled as she watched him. Alvin could feel his eyes water just from the scent of the peppers. "God, why do we even have these?" he asked himself and Eleanor laughed. He slowly lifted one out of the jar and eyed it nervously as he gulped. Then finally he blew out a quick breath as he built up enough courage to eat the first one. He closed his eyes and put it in his mouth, and then he quickly ate it.

Eleanor clapped. "Way to go, Alvie. Now you only have two to go," she said.

Alvin slowly opened his eyes and looked up at her. "Please, Eleanor," he said slowly. "Can't this be enough?"

She smiled and shook her head. "A dare is a dare, Alvin," she said.

Alvin groaned, and then took two peppers out of the jar and did the same thing he did with the first. He dropped his head on the table and screamed slightly. "God, my mouth is on fire!" he exclaimed.

Eleanor laughed and got up to get him water and bread. She placed it in front of him and he quickly ate the bread and drunk the water. Eleanor smiled at him. "That was awesome," she commented.

Alvin glared at her. "You are never giving me a dare again."

She laughed a bit. "Hey, whose idea was this?"

He rolled his eyes and took a sip of his water. "Alright, now it's my turn." He started to think of something just as bad as what she made him do. Eleanor waited patiently, wondering what he would think of. She was certain that he was going to try to make her something worse than what she made him do, so she mentally prepared herself for whatever he had to dish out.

Alvin sat back in his chair, looking around the kitchen. A moment later, Dave walked in. He pulled something out of the refrigerator. When he turned around, he finally noticed the two sitting at the table. "Oh, hi, Eleanor," he said, not even knowing that she was there.

Eleanor smiled. "Hi, Dave," she greeted with a small wave. Alvin looked at her, and then back at Dave, and then back at her. He arched an eye brow and smirked.

"Well, you two can continue with what you were doing. Nevermind me," Dave said before walking out of the kitchen.

Eleanor looked back at Alvin and noticed the look on his face. She got a little nervous. "Something tells me you have your dare," she said.

Alvin nodded slowly. "That I do," he said. He leaned forward and kissed her. "You know I love you, right?" he asked.

Eleanor eyed him suspiciously. "What do you want me to do?" she asked cautiously.

Alvin smiled and sat back in the chair. "I dare you to go in the living room and tell Dave that you have a crush on him," he declared. "And you have to do anything necessary to convince him that you'll have him one day."

Her eyes widened. "You want me to do what?!" she demanded.

"Come on, Ellie, this isn't as nearly as bad as what you made me do," Alvin said.

Eleanor nodded. "You're right, it's worse," she said and Alvin laughed. "Alvin, I can't do that. Imagine how he'll look at me from now on. Please give me another dare," she pleaded.

He shook his head. "No, I like this one," he said and Eleanor glared at him. He smiled. "Go on. The sooner you do it, the sooner it'll be over."

She sat there a moment looking extremely uncomfortable and nervous. Finally, she sighed and stood and slowly made her way to the living room. Alvin stood at the doorway of the kitchen and crossed his arms with a smirk on his face. Eleanor hesitated to approach Dave, who was busy watching TV and hadn't noticed that she had come in. After a few seconds, she built up enough courage and closed the distance between her and Dave. "Um, Dave?" she said and he looked up at her.

"Oh, hi, Eleanor. Are you taking a break from Alvin?" he asked with a smile.

She shifted her with an uncomfortable smile. "Uh, yeah, something like that." She cleared her throat. "Can I talk you about something?"

Dave sat up more straight and nodded. "Sure, you can. Is everything alright?" he asked with concern.

She sat beside him and sighed. "More or less," she said.

"Ok, well tell me what's wrong," Dave said as he turned the TV down, making sure he heard everything she had to say.

She hesitated, definitely not wanting to do this. She played with the hem of her skirt as she stared down at the floor. Dave just watched her, letting her take all the time she needed. Finally, she said, "I have a confession to make."

Dave nodded. "What is it?"

Alvin smiled from his place at the kitchen doorway. He knew he was going to enjoy this.

'Damn you, Alvin,' Eleanor thought. She couldn't believe that she was about to this. She looked up at Dave with a small smile. "I…I've always had this little crush on you," she said shyly.

Dave blinked a few times. "Um…you, you have?" he asked, starting to feel a bit uncomfortable.

She looked down and nodded. "But that was years ago," she explained and Dave felt a bit more relieved. She looked up at him again, but this time, there was no longer any shyness. "Now," she continued, "it's grown into something much more than just a little crush."

Dave's eyes widened slightly. "W-what?"

Alvin nearly burst out laughing, but he covered his mouth just in time.

Eleanor scooted closer to Dave. "That's right, Dave. I've grown to love you," she proclaimed.

Dave tried to move away from her, but the arm of the chair was in the way. "Um, Eleanor, that's really sweet, but I think you might be a little confused," he said.

Eleanor tilted her head a bit. "Why do you say that?" she asked sweetly.

Dave shook his head. "I don't think you're…in love with me. You're probably just seeking male attention seeing that you don't have a father figure around," he explained carefully, not wanting to upset her.

Eleanor smiled, and then laughed while shaking her head. "Oh, Dave, it's nothing like that," she said, placing her hand on his knee. His entire body went rigid. Eleanor looked him right in the eye with a smirk. "I know what I want and I want you. I truly believe that you're the man of my dreams and I'm determined to have you."

Dave looked a mixture of shocked, scared, and completely stumped. He shifted his eyes as he was at a loss of words.

Alvin was having an extremely tough time keeping in his laughter as he watched the whole thing take place. 'Ellie is too good,' he thought.

Eleanor smiled sweetly at Dave and put her hand on his cheek. "You just wait, dear. One day, you will be mine. I'll make sure of it." And with that, she stood and made her way back to the kitchen, leaving a tremendously uncomfortable Dave sitting there with shock written all over his face.

As Eleanor walked by Alvin, she shot him a death glare. "I hope you're happy," she growled.

Alvin chuckled. "Delighted," he said and followed her into the kitchen.

--

Well how was that? Imagine how Dave is feeling right now. And I bet his expression was priceless. Well tell me your thoughts and be sure to give me dares that you want done.

Jade


	3. Chapter 3

Ok so I know I took forever and a day to update this bugger, but school has really put it on me this year so just bear with me. Also, BrittanySeville18 helped with this chapter. Can you believe I got writer's block? But yeah, here you are.

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**Dare # 4- Lunchroom Kiss**

The Chipmunks and Chipettes were sitting at a lunch table during lunch talking about Alvin's soccer game that took place the day before.

"That was a great game, Alvin," Jeanette said. "I should go to more."

Alvin smiled. "Yes you should. No one ever gets enough of me kicking butt," he said.

Simon rolled his eyes. "You and your ego," was all he said.

Alvin shrugged. "What can I say? I'm awesome."

Theodore arched an eye brow. "I think that's only in your mind," he said and Alvin shot him a look.

Brittany smirked. "Well, it's not like he doesn't have a point."

Alvin rolled his eyes. "Did you guys just come here to insult me?" Eleanor laughed and grabbed his hand. "So, anyway, did Eleanor tell you two about the dare she did the other day?" Alvin asked Brittany and Jeanette.

"Oh, God, yes she did," Brittany said.

"I can't believe you made her do that," Jeanette said.

Alvin simply laughed. "It was just too good. You just had to see it."

Simon smiled. "Well, I don't think Dave got a kick out of it," he pointed out.

Jeanette shook her head. "Imagine how Dave is going to feel toward her from now on."

"Thank you!" Eleanor said. She arched an eye brow at Alvin. "I tried to tell him that, but no, he just would change the dare."

Alvin chuckled. "Dave will be fine. I'll tell him it was a joke," he assured her.

Eleanor shook her head. "God, Alvin, you always dish out these terrible dares."

"But you end loving them in the end," he replied.

Brittany arched an eye brow. "What you need is a taste of your own medicine," she declared.

Alvin arched an eye brow of his own. "Is that so?" He smirked.

She nodded. "That's right. Someone needs to hit you with your own trick tenfold and then maybe you'll reconsider what you dare people to do."

He sat back in his chair and crossed his arms. "Oh, that will never happen," he assured her.

A smirk appeared on Brittany's face. "Never say never because it's bound to happen one day, Seville," she said. Then she turned to Jeanette. "Make it happen, Jeanette."

Jeanette blinked and looked at her. "What?"

Alvin laughed slightly. "What?"

Theodore furrowed his eye brows in confusion. "Why Jeanette?" he asked.

Brittany did her signature flipping of her hair over her shoulder and faced him. "Well, if it was one of us, we would focus on hurting him…or at least I would." Alvin rolled his eyes. "But that won't last long at all. He needs to do something that won't hurt him, but embarrass him and keep the school talking for weeks to come." She smiled.

Jeanette shook her head. "And you think I can give him something that will cause that?" she asked, a bit skeptical.

Brittany looked at her. "Well, do you want to hurt him?"

"Um, no," Jeanette replied.

"Then give him an embarrassing dare."

Alvin smiled. "Don't worry, Jeanette, you won't embarrass me too much," he said and Eleanor rolled her eyes.

Jeanette eyed him for a moment before smiling. "I think I have the perfect dare for you," she said.

Alvin nodded with a smug smile. "Let me have it."

The rest of them listened closely. Jeanette motioned behind him. "I dare you to kiss Miss Patterson," she said.

The rest of them gasped and Alvin's smiled faded immediately. "Do what?" he asked.

Miss Patterson was their old and bitter lunch lady. She was about 60 years old and she hated kids. No one understood why she worked at the school if she disliked kids, but she did. Jeanette smiled and said, "I dare you to kiss the lunch lady."

Brittany started laughing. "Damn! Now that is a good dare," she said and Alvin glared at her.

Theodore smirked. "Well, Alvin, a dare is a dare. You have to do it."

Alvin arched an eye brow. "No I don't," he declared.

Eleanor arched an eye brow of her own. "Excuse me? You made me do that dare with Dave, so you have to do this one."

Brittany smirked. "That is, unless you're scared."

Alvin eyed her like she was crazy. "I am not scared," he said.

"Then prove it," Simon jumped in. Jeanette simply smiled.

Alvin just looked at all of them before rolling his eyes and standing. "Fine, I'll do it." They all smiled.

"Wait, Alvin, before you go," Jeanette started, "there is one little thing."

"And what's that?"

She giggled, and then said, "You have to kiss her on the lips."

After hearing that, all of them, minus Alvin, burst out laughing. "Oh, now that's cruel," Simon said between laughs. Alvin just stared at them, not finding any of this very amusing.

But he did agree with Simon as he nodded. "Yes it is, and I'm not doing it," he said.

"Alvin, don't be a bad sport," Theodore said.

Alvin rolled his eyes. "I'm not being a bad sport. That's just gross. I refuse to kiss a bitter old lady on the lips. It's freaky," he said.

Brittany smiled and looked at Jeanette. "He can't handle it," she purposely said loud enough for him to hear and Jeanette just shrugged.

"I suppose not," she replied. Eleanor smiled slightly, knowing exactly what they were doing.

Alvin frowned. "I can so!" he argued.

They looked up at him for a moment before looking back at each other and shaking their heads. Eleanor giggled and Simon and Theodore simply smiled.

Alvin's frown deepened. "You know what, fine, I'll do it, but I don't wanna hear one complaint when I give either of you a dare," he said.

"Yeah, sure, whatever, just go," Brittany said, rolling her eyes.

He blew out a breath. "Alright, here goes nothing." He then walked away from the table toward the line.

Brittany smirked and looked at Simon and Theodore. "One of you follow and take a picture to have proof that he did it," she said.

Theodore smiled and stood. "I'm on it," he said and followed Alvin.

Alvin slowly approached the lunch line and Miss Patterson. All the while, he mentally prepared himself for what he was about to do. Though he hated to do this, he had to admit that was a good dare and he was a bit shocked that Jeanette came up with one so good. He knew he had to get her back though, but he didn't have to think about it as he finally arrived at his destination. He blew out a breath. 'Ok, here goes,' he thought. Theodore stood a short distance away with his camera ready.

At the moment, Miss Patterson hadn't noticed Alvin. To make himself known, he cleared his throat. "Hey, Miss Patterson," he said casually with a smile.

Miss Patterson finally looked up and when she saw him, she did not smile. "What do you want?" she asked grumpily.

Alvin leaned on the counter. "I just wanted to see how you were doing today." He continued to smile.

Miss Patterson wasn't impressed as she just stared at him.

"Come on, Miss Patterson, I'm just trying to be nice here. Can I please get a response?" he asked sweetly.

Miss Patterson narrowed her eyes. "I've had better days," she finally said.

"Aw, well I'm sorry to hear that. Is there anything I could do to make your day better?"

"You can leave," she stated.

He chuckled and nodded. "Yes, well I know that's an option, but I really wanted to talk to you, Miss Patterson."

"I don't have time for talking."

He smiled. "Sure you do. You're not doing anything now, so why not talk to me?"

She scowled. "I don't want to talk to…"

He moved closer suddenly. "You look really nice today," he said, interrupting her.

"Go away," was all she said.

"But Miss Patterson, that's the complete opposite of what I want to do."

She glared at him. "I don't care."

He nodded. "Ok, but before I go, could I at least tell you what I want to do?" he asked.

"No," she deadpanned.

He crossed his arms and stood there. "Well, then I'm not leaving. Not until you let me tell you," he said in a childish manner.

That irritated her even more as her glare worsened. Finally, she huffed. "Fine, what do you want to do?" she asked, willing to listen to something she cared nothing for if that was the only way to get him to leave her be.

'Alright, let me get this over with,' Alvin thought and groaned inwardly. Instead of answering her question with words, as she originally thought he would (and probably would've preferred), he leaned forward and gave her a quick kiss.

Theodore's jaw dropped from shock, but he did manage to take the picture. Then he quickly went back to the table.

Alvin thought he was going to be sick, but he managed to keep his cool as he smiled at her. "Bye, Miss Patterson," was all he said and he turned and left, leaving a frozen lunch lady.

Alvin walked back to the table and sat down looking extremely calm. He was also very quiet. Everyone stared at him with smiles on their faces. "So…" Eleanor started.

Before she could finish, Alvin raised his hand and shook his head, telling her not to say a thing to him.

They eyed him.

"Are you o-," Simon started, but Alvin did the same thing to him.

Alvin lowered his hand slowly, and picked up his fork. He picked at his salad. Once he had a decent amount, he lifted it to eye level. Everyone still watched him, silent.

"I think my dare was a little too much for him," Jeanette whispered.

Alvin's mind soon processed what he did. 'I kissed the lunch lady!' With that thought playing repeatedly, his eyes rolled back into his head and he fell out of his chair onto the floor, passed out.

Everyone jumped in surprise once he hit the floor, and then stared at him. "I think you're right," Simon said a moment later.

--

Ok how was it? Was it worth the wait? Be sure to keep the dares coming. I already have two more dares that I gotta write but I still want more.

Jade


	4. Chapter 4

**Dare #5 – Maid Outfit**

Alvin sat on his bed thinking of a way to get Jeanette back. He'd been trying to erase the memory of him kissing Miss Patterson. He shuddered slightly. _Disgusting_. But he had to admit, though, it was a good dare. So, he had to give her something even worse.

He lay back and stared up at the ceiling. "What could I make her do that would take her out of her comfort zone?" he asked himself. He knew she was pretty timid, so it wouldn't take too much to embarrass her. But he needed something good.

After a long while of thinking, a light bulb went off in his head and he sat up with a big smile like he had had an epiphany. He quickly grabbed his cell and dialed Jeanette's number.

She answered on the third ring. "Hello?"

"Jeanette," he started enthusiastically, "I need to talk to you."

"Well it would seem that way seeing that you called me," she responded.

Alvin rolled his eyes. "No need for smart comments, thank you," he said.

She laughed a bit. "Ok, I'm sorry. What do you need to talk to me about?" she asked, getting back on the subject.

He smiled. "I've been thinking," he started.

"Uh-huh…"

"And I've come up with a perfect dare for you," he concluded.

"A perfect dare?" was her surprised response. "You're daring me?"

He smirked. "Well of course. I just have to get you back for that God awful dare." There was silence on the other end, and Alvin couldn't help but laugh. "Well do you wanna hear it now or do you want me to text it to you?" He laughed again.

He heard Jeanette huff. "Sure, Alvin, let me hear it," she said, and Alvin could hear the reluctance in her voice.

"Ok, now don't freak out," he advised, but he knew she would.

"Just tell me what it is, please."

He smiled. "I dare you to wear a French maid outfit to school," he proclaimed.

"You want me to do what?!"

He laughed. "That's funny. Eleanor said the exact same thing when I gave her that other dare."

"Alvin, I'm not doing that," Jeanette stated defiantly.

"Yes you are. A dare's a dare, Jeanette. You gotta do it."

"But –,"

"Nuh-uh, no complaints, like I said when you made me kiss Miss Patterson," he shuddered. "Besides, it's not that bad. It's just another outfit. It's just a little more…provocative." He smiled.

Jeanette sighed, and after a moment she asked, "But what if I get in trouble?"

"I'll make sure that doesn't happen," Alvin assured her as he lay back on his bed again. "Now, there's one other thing."

"And what's that?"

"You have to wear it for at least half the day," he explained.

"Alvin," she groaned.

"Come on, Jeanette, this isn't that bad. What you made me do is gonna scar me for life. What I'm making you do won't do anything but get you more attention. How bad could that be?"

--

Jeanette listened to Alvin, a little apprehensive with his dare.

"Come on, Jeanette, this isn't that bad. What you made me do is gonna scar me for life. What I'm making you do won't do anything but get you more attention. How bad could that be?"

She sighed, not knowing what to say. She knew he wasn't going to let up on this. "…Ok, Alvin," she finally agreed.

She could practically hear him smile on the other end. "Great! And don't worry about a thing. I'll provide the outfit," he said.

Her eyes widened a bit. "Um…should I trust you with that?"

He chuckled. "Don't worry, Netta. I'll get you something within the dress code…just barely," he said, and chuckled again.

--

The next morning, Alvin knocked on the Miller's door. He had a smile on his face, and he held a bag by a hanger in his hand.

Awhile later, the door swung open and Eleanor was in view. She smiled once she saw Alvin. "Hey," she said as she opened the door wider to let him in.

He smiled. "Hey, babe," he said as he stepped in and gave her a peck on the lips.

She giggled lightly as she closed the door. That's when she noticed the bag. "Ooh, is that for me?"

He chuckled. "Actually, it's for Jeanette."

She arched an eye brow. "It's for Jeanette?"

He nodded. "It's for a dare," he explained.

"Oh…I see," she said while nodding.

At that moment, Jeanette and Brittany came downstairs. Brittany rolled her eyes once she saw Alvin. "Oh goodie, look who's here," she said.

Alvin smiled sweetly. "Good morning to you too, Brittany," he said in the same manner.

"Yeah whatever," she replied.

Jeanette noticed the bag in Alvin's hand and she froze. "Please tell me that's for Eleanor," she begged as she eyed the bag.

Alvin shook his head with a smirk as he approached her. "Nope, sorry, Jeanette, this is for you." He held out the bag for her.

She sighed in disappointment, reluctantly took the bag, and headed back upstairs.

Eleanor then walked over to Alvin and grabbed onto his arm. "So what is it?" she asked in curiosity.

Alvin smirked down at her as he put his arm around her. "You'll see when we get to school."

--

The Chipmunks and Chipettes soon arrived at school. Everyone, excluding Alvin, was curious of what Jeanette was wearing under her trench coat. She also seemed to look a bit uneasy the entire walk to school.

They walked inside, and for some reason, it seemed to Jeanette like everyone had chosen that day to be out in the hall. She groaned really not wanting to do this dare now. She went to her locker trying to ignore the stares. While she was getting the things for her class, Alvin walked up to her.

"I really can't wait for this to start," he said with a smirk as he leaned against the locker beside hers.

Jeanette glanced at him. "You are so terrible. I can't believe you're making me do this," she said.

He arched an eye brow. "Am I terrible? I do believe you're worse than me."

She huffed and rolled her eyes. "Well you didn't have to get me one so short."

He smirked. "Oh it is not that short. Now stop stalling and get to it. The sooner you start, the sooner it'll be over."

She sighed. At that moment, Eleanor walked up. "Ok, Jeanette, what is under the coat?" she asked.

Alvin smiled as he put his arm around Eleanor. "Oh, you're about to see in a few minutes," he said.

Jeanette huffed. "Fine," she said, and shoved her books in his arms, causing him to chuckle. Then she slowly undid the buttons. Finally, once all the buttons were undone, she slowly slid off the coat.

Eleanor gasped at seeing her sister wearing a French maid outfit. "Oh my goodness, Jeanette? Alvin, what have you done? I can't believe you dared her to do that," she said, staring up at him.

Jeanette sighed as she put her coat in her locker and shut the door. "You and me both," she said. She then took her books from Alvin.

Alvin just smiled. "Well get going. You gotta go to class…which happens to be on the other end of the building."

Jeanette groaned. "Oh my God," she mumbled. Then she turned reluctantly and started slowly walking down the hall.

Alvin couldn't help but laugh. "This is gonna be good."

Eleanor just stared at him.

--

As Jeanette walked to class, the stares from before were a lot worse than before. She could hear murmurs, and it made her blush to no end.

"Oh my God…" she heard one person whisper.

"Can you believe this?"

"No…way…"

"Why is she wearing that?"

Suddenly, someone yelled out, "Lookin good, Jeanette!"

Her blush deepened, and she wanted nothing more than to get to class.

Suddenly, she bumped into someone, seeing she wasn't looking up. But she did look up and her eyes widened because the principal was staring back at her. She took a few steps back.

Looking her over with an arched eye brow, the principal, Mr. Schumacher, said, "That's quite an interesting outfit, Jeanette."

Jeanette shifted her eyes. "Um…" She looked around, and saw everyone standing around watching. This was exactly what she was afraid would happen.

Suddenly, she felt an arm go around her shoulders. "Mr. Schumacher, how's it going?" followed Alvin's voice.

Mr. Schumacher looked at him. "Hello, Alvin."

Alvin smirked as he glanced at Jeanette. "So, I see you were admiring Jeanette's new style," he said.

Mr. Schumacher arched an eye brow. "I'm not admiring it. I was actually about to advise her to change immediately," he corrected.

Jeanette looked down.

That comment, however, didn't phase Alvin one bit. "Why would you do that? She's completely within dress code," he said with a confident smile.

"Actually, I don't think…"

"…Is her outfit see-through?" Alvin cut in.

Mr. Schumacher was about to reply, but once he looked at her outfit again, he stammered a bit. "W…well, no…but…"

Alvin arched an eye brow. "Is she showing any under garments?"

Mr. Schumacher huffed. "No."

Alvin nodded. "Well I think this outfit is allowed. Now if you would excuse us, we have to get to class." And with that, he led Jeanette away from him.

Jeanette sighed in relief. "Thanks, Alvin."

He smiled. "I told you I wouldn't let you get in trouble. Now you go strut your stuff all the way to class." Then he walked away.

Jeanette shook her and continued to class.


	5. Chapter 5

**Dare #6 – Phone Operator**

The guys were sitting around the house that weekend with nothing to do. They were all hanging out in the living room, Alvin flipping through channels on the TV and Simon and Theodore staring completely bored.

After going through a few more channels Alvin threw the remote down. "Ok, this is ridiculous," he stated.

Simon stared at him. "I was wondering when you would finally realize that," came his jaded voice.

Alvin glanced at him before rolling his eyes. "We gotta do something. I'm tired of just sitting here," he complained.

Theodore shrugged. "Well what do you propose we do?"

Alvin let out a breath. "Don't you think if I knew I would tell…" he trailed off as he began to think. After a moment, he abruptly pointed at Theodore. "…You."

Theodore blinked and shifted his eyes. "What?" he asked in confusion.

Simon raised a brow as he watched. Sometimes he just didn't understand Alvin.

Alvin smirked. "Truth or dare?" he then asked.

Simon rolled his eyes. "This again?"

Alvin narrowed his eyes at him. "Shut up, Si." He then looked back at Theodore. "Well?"

Theodore raised a brow. "What makes you think I want to play?"

Alvin stared at him for a moment before rolling his eyes. "Just choose one already," he said, ignoring the question.

Theodore stared at him for a minute, and then sighed. "Dare," he finally said.

Alvin smiled, glad he chose a dare. "Awesome." He then began to think of a good one. After a moment, he smirked and looked back at Theodore. Then he grabbed the cordless phone and held it out to him. "I dare you to flirt with the phone operator," he told him.

Theodore stared at him like he was crazy, as did Simon. "I most definitely will not," he said defiantly.

Alvin laughed. "Come on man, it's not hard. Just a few lines until she hang up on you."

Simon raised a brow. "And what if it's not a woman?" he asked.

Alvin simply smiled but didn't answer the question. He just tossed the phone to Theodore. "Have at it," he said.

Theodore rolled his eyes and picked up the phone. He then dialed the phone operator, and as it rung he put it on speaker so Alvin and Simon could hear.

Soon they heard a female's voice say, "Operator, what number can I connect you to?"

"I'd like to be connected to you, baby," Theodore said, deepening his voice as he tried to sound sexy.

Alvin suppressed his laughter while Simon smirked and raised an amused brow.

"Um…excuse me?" the woman asked.

Theodore smiled. "You heard me, baby. How would like to get to know a fine specimen like myself?" He had to keep himself from laughing at that.

Alvin chuckled lightly to himself while Simon shook his head with a smile.

The woman was silent for a moment. "Um…sir, I don't think this is…"

"What's your name, sweetheart?" Theodore interrupted.

"Uh…Cindy," she answered.

"Such a pretty name for such, I'm sure, a pretty girl. Well Cindy, you can call me Cupid and I'm here to put my spell on you."

Alvin almost died from laughter at that but he kept himself together. Simon couldn't help but to chuckle at that. Even Theodore had to keep himself laughing out loud.

"Excuse me, sir, but I think you've called the wrong operator," Cindy tried.

Theodore chuckled. "No, I think I've called the right one. So how would you like to get to know me, pretty lady?"

Cindy was starting to get a little impatient. "I would not like to get to know you," she stated.

"Aw, but wouldn't you? I promise I won't bite…unless you ask me to."

"Excuse me? I don't think so!"

"Suit yourself," Theodore smiled, "but I'm not giving up. So what do you say? Me, you, and a bucket of chocolate covered strawberries in a candle lit room?"

"I'm terminating your call now, sir," Cindy said, returning to her professional persona.

"Come on now, sexy…"

The line went dead and all three of them fell out laughing.

"Yo, that was crazy," Alvin stated between laughs.

Simon smirked. "I can't believe you pulled it off," he said to Theodore.

Theodore continued to laugh. "It was nothing."

Alvin shook his head. "That was perfect. I must dare you more often," he concluded.

Theodore arched a brow. "Uh, no thanks."

Alvin smiled. "Oh, no, you've started something now."

Simon arched a brow. "Alvin, you might want to be careful who you dare. Wouldn't want another incident like Miss Patterson, would you?" he chuckled.

Alvin shuddered a bit as a reflex. "That was not funny," he grumbled.

Theodore laughed. "Oh, but it was," he said.

Alvin rolled his eyes. "Whatever." He looked at Simon. "Just for bringing that up, you get the next dare."

Simon simply shook his head. "No, thank you. I'd rather not participate in your game."

Alvin smirked. "If you say so…"

xxxxx

What does Alvin have in store for Simon? You'll find out soon enough. Meanwhile, tell me what you think!


	6. Chapter 6

Well this is the last chapter. Hope you liked the story! Here you go…

xxxxx

**Dare 7 – Hard Times**

The Chipmunks and Chipettes were all spending a day in the park. They all sat together at a picnic table engaged in their own separate conversations.

"So," Brittany said to Theodore, "I heard about your little escapade with the phone operator."

Theodore laughed a bit. "It wasn't a big deal. It was just a little dare."

"Yes, I know," she said, "Mr. Cupid."

He laughed again as he scratched the back of his head. "Yeah…"

Across from them sat Alvin and Eleanor, who were talking to Simon and Jeanette. "I've been thinking about your dare, Simon," Alvin told him.

Simon stared at him indifferently. "I thought I told you I wasn't doing any of your dares," he said.

Eleanor smiled. "Aw, why not? It's all for fun."

Jeanette nodded. "I even did one…if you can remember."

They all laughed, catching the attention of Theodore and Brittany. "What's so funny?" Brittany asked.

"Alvin wants to give Simon a dare," Jeanette replied.

Theodore nodded. "That's right. He is the only one that hasn't had one yet."

Simon arched a brow. "And I'll be the only that doesn't have one," he stated as-a-matter-of-factly.

Alvin smirked. "What's wrong with a little dare, Si? Like Ellie said, they're all for fun."

Simon just stared at him.

"Tell you what," Alvin said, "You do one little small dare and you won't have to do another one."

Theodore smiled. "Yeah, come on. It'll be fun."

Simon remained still and silent for a moment before sighing. "Alright, fine, I'll do one dare," he finally agreed.

Alvin laughed. "Alright, cool. Like I said earlier, I've been thinking about a dare for you and I think I've got the perfect one."

Simon raised an apprehensive brow. "I'm not sure if I made a good decision."

Eleanor laughed. "Oh, I'm sure it won't be too bad. Right?" she asked Alvin.

Alvin shrugged and waved it off. "Oh, it's simple."

Simon continued to give him that look. "And it is?"

Alvin smirked. "All you have to do is go up to some people pretending you're homeless and ask for spare change."

Simon stared at him. "I knew I made the wrong choice."

They all laughed. "Oh, it's not that bad," Alvin said. "Just do it. It'll only take a couple of minutes."

He sighed as he looked around. Luckily there weren't many people around. He then stood. "Fine." He then walked off to find someone.

Alvin smirked as they watched him. "This is gonna be good."

As Simon walked away, he tried to change his appearance a little. He ruffled up his hair and untucked his shirt. He figured he looked alright and finally spotted a couple at a pond. He shook his head before going over to them. "Ex…excuse me…" he said innocently.

The two turned around. "Can we help you?" the man asked.

Simon cleared his throat. "Uh, forgive me for the sudden intrusion. But um…that is…if it's not too much to ask, could you by any chance have any spare change? I have not had my daily intake of nutrients in days."

The man and woman looked at each other, not sure they believed him. They looked back at him, looking him over. The woman then spoke. "Wait…aren't Simon Seville? Part of that band…Alvin and the Chipmunks?" she questioned.

Simon nodded. "Yes, well there have been a lot of problems. You see, my brothers and I have been dropped from our label and now, unfortunately, times are quite hard for all of us."

The man cleared his throat. "Oh you got dropped from your label? That's um…"

"That's really too bad," the woman finished.

Simon nodded. "I mean it when I say that I hate to do this. I'm sure the last thing you wish to do is give your hard earned cash to me but…"

"It's no problem," the woman interrupted. The man looked at her in surprise and she shrugged. "Honey, it's the least we could do," she urged.

The man sighed before reaching in his back pocket and pulling out his wallet. A moment later, he held a five dollar bill out to him while putting his wallet back in his pocket. "Here you go."

Simon arched a brow, a little surprised they were actually doing this. He then took the bill, smiling gratefully at them. "Thank you so much," he said before walking off in the direction he came. After walking a little ways, he glanced back to see the couple walking away, obviously talking about what just happened. Simon shook his head before turning back around.

At the table, the rest of them watched with smiles. "I wonder what he told them," Jeanette said.

Alvin smirked. "We'll see when he gets back."

A moment later, Simon took his place back at the table after first fixing his shirt and hair. "Well, that was quite easy," he concluded.

Theodore smiled a bit. "So, what'd you tell them?"

Simon shrugged. "That we were dropped from the label. The lady fed right into it," he said.

They fell out laughing. "Like that'll happen," Alvin stated.

Simon smirked. "Well in case it does, I have five dollars to get me started," he chuckled.

They laughed again.

They would have to do dares more often.

xxxxx

Well that concludes this story. It was fun. Hope you enjoyed it. Until next time…

Jade


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